Institute of Chemical Research of Catalonia

Catalytic process for the preparation of carboxylic acids from haloalkanes or alkenes.

Posted by Frederic from Institute of Chemical Research of CataloniaResponsive · Patents for licensing · Spain

Summary of the technology

A convergent process for the preparation of terminal carboxylic acids by carboxylation of mixtures of bromoalkenes or mixtures of olefins has been developed. The process is catalytic in nickel and allows preparing a unique product from a mixture of starting materials (regioconvergent process), which allows saving several synthetic and separation steps in processing and renders possible the use of the process with exhaust streams from crackers. The process is useful for the production of fatty acids.

Description of the technology

The ability to effectively recycle bulk materials into highly valuable products from simple chemical feedstock represents an important and critical contribution for our circular economy. In line with this notion, selective functionalization of simple and available unactivated olefins, products that are manufactured on large scale during petroleum processing, is becoming one of the world´s most important and demanding challenges since the petrochemical, detergent and fragrance industry and a myriad of biological relevant molecules are mainly based on aliphatic hydrocarbon side-chains. Taking into consideration the ubiquity of hydrocarbons and the lack of current methods for selectively activating these frameworks, a step-economical project devoted to achieve these goals will have crucial implications for our society. Indeed, current methodologies for the selective functionalization of hydrocarbons are primarily based on lengthy synthetic sequences that necessarily require prefunctionalization techniques at a specific reaction site, thus not representing an added value from an industrial, atom- and step-economical standpoint. Therefore, the design of an efficient, robust, sustainable and inexpensive technique for functionalizing selectively hydrocarbons represents a highly rewarding scenario for industrial laboratories.

We have recently discovered a catalytic reductive carboxylation of abundant, inexpensive and unactivated olefins and bromoalkanes with CO2 for preparing hydrocarbons bearing a carboxylic acid on the side-chain. Specifically, we have found that a statistical mixture of different isomers of octene can all converge to exclusively nonanoic acid in good overall yield. Importantly, the protocol is user-friendly, operationally simple, with components that are neither air- nor moisture sensitive and operates under mild conditions using earth-abundant catalysts and without requiring pre-functionalization at specific reaction sites. All these unique features make such a protocol particularly attractive for its implementation at large scale en route to industrially-valuable fatty acids by minimizing the number of steps and wasteful reagents since chemists will not need to make a significant effort to purify mixtures of olefins/bromoalkanes derived from petroleum processing.

Main features:

Specifically, the innovation potential ofthe technology consists of the following:

  1. Significant step-forward for our circular economy:: recycling of CO2 with bulk materials derived from petroleum processing for preparing fine-chemicals
  2. Innovative new CO2 fixation for preparing carboxylic acids: Unlike industrial methods based on hydroformylation techniques with highly toxic CO and expensive noble catalysts (Rh), hydrolysis of nitriles (toxic cyanides required) or oxidative protocols of pre-oxidized alcohols, the technology will describe an unconventional catalytic protocol for easily and rapidly preparing carboxylic acids from abundant, and cheap feedstock.
  3. Industry-friendly conditions: The reaction conditions are user-friendly, operationally-simple and the protocol is based on air- and moisture insensitive materials. Additionally, hydrophilic carboxylic acids are easily separated
  4. Economically-viable: cheap and abundant reagents are used. Importantly, single carboxylic acids are obtained from isomeric mixtures of unrefined olefins, a feature of utmost importance that will reduce costs at large-scale.
  5. Efficiency: No byproducts are generated.
  6. Sustainable

Business opportunity:

Carboxylic acids are primarily used in the manufacture of soaps, detergents, pharmaceuticals, rubber, plastics, dyes, textile, perfumes, and animal feed. The global carboxylic acid market was valued at US$ 12.14 Bn in 2014 and is anticipated to reach US$ 18.49 Bn by 2023, expanding at a CAGR of 4.9% between 2015 and 2023. In terms of volume, the global carboxylic acids market stood at 17.82 million tons in 2014. Rising demand for carboxylic acids derivatives is anticipated to boost the global market in the years to come.

Current development status

Experimental technologies

Applications

manufacture of carboxylic acids

Applications

valorization of cracking exhaust streams

Desired business relationship

Patent licensing

Technology development

New technology applications

Other : joint technology development

Intellectual property status

Patent already applied for

Patent application number : EP17165736

Where : Europe

Intellectual property status

Patent already applied for
EP16382336
Europe

Patent already applied for
EP17165736
Europe

Technology Owner

Institute of Chemical Research of Catalonia

Technology Transfer Office

Additional information (attached documents)

Related keywords

  • Industrial Technologies
  • Process Plant Engineering
  • Chemical Technology and Engineering
  • Organic Substances
  • Soaps, detergents
  • Physical Sciences and Exact Sciences
  • Chemistry
  • Organic Chemistry
  • Petrochemistry, Petroleum Engineering
  • Industrial Products
  • Chemicals and Materials
  • Industrial chemicals
  • Other chemicals and materials (not elsewhere classified)

About Institute of Chemical Research of Catalonia

Technology Transfer Office from Spain

The Institute of Chemical Research of Catalonia represents one of the very first fruits of the new scientific policy of the government of Catalonia (Spain) aimed at creating new research centres in strategic areas. ICIQ, in particular, has been created with the ambition of becoming a reference for chemistry in the European Research Space. Our society faces important challenges in the XXI century, among which health and environmental concerns are of outmost importance. Chemistry will play an essential role in both of these challenges. To succeed, our increasingly knowledge-based economy will require a solid and strong chemical industry; currently 150.000 jobs in Catalonia (and more than 2 million in the EU) directly arise from the chemical industry. In order for this industry to be successful in the future, it must take a sustainable approach based on the rational use of feed-stocks and raw materials. For this, fundamental chemical research needs to be funded and novel approaches into transforming matter must be developed. We at ICIQ consider that catalysis is the key activity for sustainable chemistry. Catalytic processes can minimize raw materials and energy consumption, and can lead to the selective formation of target products with minimal generation of wastes. In line with this consideration, we have taken catalysis as one of our main research topics. Complementary to our research focus, attention has been paid to the development of a simple and efficient organizational model for ICIQ, able to overcome known difficulties normally associated with larger and more traditional research institutions. The Institute of Chemical Research of Catalonia aims at bridging the gap between academic research and industry, focusing its research on catalytic chemical processes for applications in health, energy and sustainability. At ICIQ, we consider that patents are highly efficient, safe and solid tools to provide protection from competitors. This is why we file patents for our in-house developed-technologies: to give our co-development projects with industry a strong starting IP position. As a research centre our goal is always to co-develop our technology adapting it to the industrial partner’s specific needs and ultimately transfer the technology to this company, with a flexible licensing strategy adapted to each case.

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